WO2012114357A1 - Process for preparing hyperbranched polyestersfield of the invention - Google Patents
Process for preparing hyperbranched polyestersfield of the invention Download PDFInfo
- Publication number
- WO2012114357A1 WO2012114357A1 PCT/IN2012/000125 IN2012000125W WO2012114357A1 WO 2012114357 A1 WO2012114357 A1 WO 2012114357A1 IN 2012000125 W IN2012000125 W IN 2012000125W WO 2012114357 A1 WO2012114357 A1 WO 2012114357A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- catalyst
- range
- acid
- reaction
- double
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 96
- 229910052751 metal Inorganic materials 0.000 claims abstract description 38
- 239000002184 metal Substances 0.000 claims abstract description 38
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 24
- 229920005862 polyol Polymers 0.000 claims abstract description 24
- 150000003077 polyols Chemical class 0.000 claims abstract description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 67
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 40
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 229920000728 polyester Polymers 0.000 claims description 33
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 239000001384 succinic acid Substances 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- 239000001361 adipic acid Substances 0.000 claims description 11
- 235000011037 adipic acid Nutrition 0.000 claims description 11
- -1 Zn2+ ions Chemical class 0.000 claims description 7
- 239000011949 solid catalyst Substances 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 2
- 229920006150 hyperbranched polyester Polymers 0.000 abstract description 32
- 230000035484 reaction time Effects 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 16
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- 238000005119 centrifugation Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000001879 gelation Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- 229910020521 Co—Zn Inorganic materials 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920000463 Poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol) Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000000024 high-resolution transmission electron micrograph Methods 0.000 description 2
- 229920000587 hyperbranched polymer Polymers 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000696 nitrogen adsorption--desorption isotherm Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000003930 superacid Substances 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- LNPQMDSMIGLHSR-UHFFFAOYSA-N 2-oxaspiro[3.5]non-5-ene-1,3-dione Chemical compound O=C1OC(=O)C11C=CCCC1 LNPQMDSMIGLHSR-UHFFFAOYSA-N 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HSSJULAPNNGXFW-UHFFFAOYSA-N [Co].[Zn] Chemical compound [Co].[Zn] HSSJULAPNNGXFW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920000229 biodegradable polyester Polymers 0.000 description 1
- 239000004622 biodegradable polyester Substances 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940124447 delivery agent Drugs 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/26—Cyanides
-
- B01J35/647—
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12715442.5A EP2678370B1 (en) | 2011-02-23 | 2012-02-23 | Process for preparing hyperbranched polyesters |
| CN201280018710.6A CN103476824B (zh) | 2011-02-23 | 2012-02-23 | 制备超支化聚酯的方法 |
| US14/001,322 US9334361B2 (en) | 2011-02-23 | 2012-02-23 | Process for preparing hyperbranched polyesters |
| BR112013021671A BR112013021671A2 (pt) | 2011-02-23 | 2012-02-23 | processo para a preparação de um campo de poliéster hiper-ramificado da invenção |
| RU2013142982/04A RU2596831C2 (ru) | 2011-02-23 | 2012-02-23 | Способ получения сверхразветвленных полиэфиров |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN471/DEL/2011 | 2011-02-23 | ||
| IN471DE2011 | 2011-02-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2012114357A1 true WO2012114357A1 (en) | 2012-08-30 |
| WO2012114357A8 WO2012114357A8 (en) | 2013-10-10 |
Family
ID=45976982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2012/000125 WO2012114357A1 (en) | 2011-02-23 | 2012-02-23 | Process for preparing hyperbranched polyestersfield of the invention |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9334361B2 (zh) |
| EP (1) | EP2678370B1 (zh) |
| CN (1) | CN103476824B (zh) |
| BR (1) | BR112013021671A2 (zh) |
| RU (1) | RU2596831C2 (zh) |
| WO (1) | WO2012114357A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013175509A1 (en) | 2012-05-22 | 2013-11-28 | Council Of Scientific And Industrial Research | Process for preparing biodegradable lubricant base oils |
| CN110922676A (zh) * | 2019-10-30 | 2020-03-27 | 中化石化销售有限公司 | 一种发泡剂母粒的制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY173189A (en) * | 2015-10-07 | 2020-01-03 | Malaysian Palm Oil Board | Metal-incorporated hyperbranched polyester-polyol |
| CN109763188B (zh) * | 2018-12-13 | 2020-06-12 | 东华大学 | 含超支化型杂化多孔材料的纤维及其制备方法 |
| CN109706535B (zh) * | 2018-12-13 | 2020-08-14 | 东华大学 | 含超支化聚合物的聚丙烯腈纤维及其制备方法 |
| CN114835911B (zh) * | 2022-05-18 | 2023-11-03 | 中南民族大学 | 山梨醇型超支化聚酯、制备方法、应用及聚丙烯复合材料 |
| CN115710348B (zh) * | 2022-09-28 | 2023-09-12 | 北京工商大学 | 微晶纤维素接枝端羟基超支化聚酯的制备方法及应用 |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0799279A1 (en) | 1994-12-21 | 1997-10-08 | Perstorp Ab | A thermosetting material |
| US6359101B1 (en) | 1999-12-15 | 2002-03-19 | Synuthane International, Inc. | Preparing polyether polyols with DMC catalysts |
| US6441126B1 (en) | 1999-04-26 | 2002-08-27 | Eastman Chemical Company | Branched aliphatic polyesters |
| US6624286B2 (en) | 1997-10-13 | 2003-09-23 | Bayer Aktiengesellschaft | Double-metal cyanide catalysts containing polyester for preparing polyether polyols |
| US6852663B2 (en) | 2001-05-07 | 2005-02-08 | Bayer Aktiengesellschaft | Double-metal cyanide catalysts for preparing polyether polyols |
| US6953765B2 (en) | 2001-05-07 | 2005-10-11 | Bayer Aktiengesellschaft | Double metal cyanide catalysts for preparing polyether polyols |
| EP1733788A1 (en) | 2005-06-16 | 2006-12-20 | Council Of Scientific & Industrial Research | An improved process for the preparation of lubricants by using double metal cyanid catatysts |
| US20080108719A1 (en) * | 1999-10-25 | 2008-05-08 | Geiger Eric J | Phthalic Anhydride Based Polyester-Ether Polyols and Double Metal Cyanide Catalyst System for Preparing Same |
| DE102008004343A1 (de) | 2007-01-19 | 2008-07-24 | Basf Se | Verfahren zur Herstellung von Polyesteralkoholen |
| US7482480B2 (en) | 2005-10-10 | 2009-01-27 | Council Of Scientific & Industrial Research | Process for the preparation of hydrocarbon fuel |
| CN101570595A (zh) | 2009-05-22 | 2009-11-04 | 浙江大学 | 含聚酯链节和聚碳酸酯链节的三元共聚物及其合成方法 |
| US20100048813A1 (en) | 2006-11-14 | 2010-02-25 | Basf Se | Highly-branched or hyper-branched polyester and the production and application thereof |
| US7754643B2 (en) | 2005-10-07 | 2010-07-13 | Council Of Scientific & Industrial Research | Transesterification catalyst and a process for the preparation thereof |
| WO2011075343A1 (en) | 2009-12-17 | 2011-06-23 | Dow Global Technologies Inc. | Ethylene oxide capping of secondary hydroxyl polyols |
| WO2011137011A1 (en) | 2010-04-29 | 2011-11-03 | Dow Global Technologies Llc | Hybrid polyester-polyether polyols |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5767323A (en) * | 1995-12-22 | 1998-06-16 | Arco Chemical Technology, L.P. | Process for preparing polyoxyalkylene polyether polyols having low levels of transition metals through double metal cyanide complex polyoxyalkylation |
-
2012
- 2012-02-23 US US14/001,322 patent/US9334361B2/en active Active
- 2012-02-23 EP EP12715442.5A patent/EP2678370B1/en not_active Not-in-force
- 2012-02-23 WO PCT/IN2012/000125 patent/WO2012114357A1/en active Application Filing
- 2012-02-23 BR BR112013021671A patent/BR112013021671A2/pt not_active IP Right Cessation
- 2012-02-23 RU RU2013142982/04A patent/RU2596831C2/ru not_active IP Right Cessation
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013175509A1 (en) | 2012-05-22 | 2013-11-28 | Council Of Scientific And Industrial Research | Process for preparing biodegradable lubricant base oils |
| US9174919B2 (en) | 2012-05-22 | 2015-11-03 | Council Of Scientific And Industrial Research | Process for preparing biodegradable lubricant base oils |
| CN110922676A (zh) * | 2019-10-30 | 2020-03-27 | 中化石化销售有限公司 | 一种发泡剂母粒的制备方法 |
| CN110922676B (zh) * | 2019-10-30 | 2022-09-16 | 中化石化销售有限公司 | 一种发泡剂母粒的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103476824A (zh) | 2013-12-25 |
| EP2678370A1 (en) | 2014-01-01 |
| US9334361B2 (en) | 2016-05-10 |
| EP2678370B1 (en) | 2016-03-30 |
| CN103476824B (zh) | 2015-06-17 |
| BR112013021671A2 (pt) | 2016-11-01 |
| US20130331542A1 (en) | 2013-12-12 |
| RU2596831C2 (ru) | 2016-09-10 |
| RU2013142982A (ru) | 2015-03-27 |
| WO2012114357A8 (en) | 2013-10-10 |
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